A collection of illustrated, humiliating short stories

Mikey is dressed as a baby girl

“I told you what would happen if you were a naughty boy, didn’t I, Mikey?”

The poor boy could only hang his head in shame. He was twenty years old, but there he was, lying on his bed wearing just a nappy. He looked so embarrassed I almost felt sorry for him. Almost.

“So, Mikey, what did I tell you would happen if you were a naughty boy?”

He still couldn’t bring himself to speak, so I thought I’d give him some extra encouragement.

“It’s no good pretending this isn’t happening, Mikey.” I said. “If you don’t answer me you're going to find yourself across my lap again for another spanking. And you don’t want another spanking, do you, Mikey? I bet your poor bottom is still quite sore from your last spanking.”

“Please,” he begged, “please don’t do this to me.”

I laughed. “Oh, Mikey! It’s far too late for that. I told you you needed to be punished, and punished you will be! Now, what did I tell you would happen if you were a naughty boy?”

Still he hesitated. I took a step towards him and gave him two hard smacks, one on each thigh. As I was so close to him I took the opportunity to pull his nappy up nice and tight around his bottom, before gently patting him on the front of his nappy. Even from such fleeting contact, and even through his nappy, I could tell that he was enjoying his humiliation quite a lot more than he was letting on.

“You have one more chance to answer my question, Mikey, before you find yourself across my lap again. And this time it’ll fifty spanks with my hairbrush, not the ten you received from my hand earlier. Now, what did I tell you would happen if you were a naughty boy?”

Clearly defeated he swallowed hard before replying “You told me I’d be treated like a baby if I couldn’t behave like a grown up, Miss.”

“That’s right, Mikey,” I smiled. “I told you you’d be treated like a baby. But not just a baby, was it, Mikey? What did I specifically say to you?”

He stared at his bare chest, inevitably looking at the babyish nappy he’d been made to wear.

“You told me I’d be treated like a baby girl, Miss,” he mumbled.

“That’s right, Mikey! I told you you’d be treated like a little baby girl. Well, you’ve got your nappy on. What else does a little baby girl need to wear?”

I watched as the tears welled up in his eyes, and started to trickle down his cheeks. I was enjoying his utter humiliation, and was determined to press home the domination I had over him.

“Perhaps I can help you here, Mikey,” I said. I held up the pair of frilly baby knickers I’d got for him. They were white, with pale pink down the middle of the front, with lacy frills around the leg holes and waistband. “Are these the sort of knickers a baby girl would wear over her nappy?”

The tears kept on falling as he tried to avoid looking at me, or at the knickers he knew he was about to be put into.

“Well, Mikey. Are these the sort of knickers a baby girl should wear?”

Shamefully, and not wanting another spanking on his still tender bottom, he meekly nodded.

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Boy in nappies 9 months ago 2